From Paralysis to Purpose in 90 Days

Recently, I challenged myself to commit to a gig by February 1 (see timer courtesy of Crushpath). My readers sent a lot of great feedback, questions…and a few very concerned head shakes. Some wanted to understand how I’m narrowing and filtering the options so that I’d be sure my next step was the right one. So with full-warning that this post is a bit of a selfie, here’s a snapshot of my process.

Getting to Know the Older Guy

Prior to starting the 90-day timer, I spent some time on what gets me up in the morning. Earlier in life, motivations were pretty straightforward (beer, money, opposite sex, beer), but with age, they’ve become more complicated. After seeing a pattern of ex-execs jump at the next “shiny metal object” job that came their way, I decided to dig deeper in the hopes of avoiding the wrong thing.

In a society infatuated with the self, there’s no shortage of tools designed to help people understand what makes them tick: Enneagram (I’m a 3), Myers-Briggs (ENTP), What Color is Your Parachute (mauve). I was even given a set of purpose cards (worst poker game ever). You could get caught up running self-diagnostics for months, but I think it’s best to pick one or two frameworks that fit your personality. Ultimately I found the most insights by asking myself: 1) When do you feel the most alive and why? 2) What do you want your legacy to be? 3) Who do you “want in the boat” with you?

I’ll spare you the navel-gazing details, but what I learned was this: I’m at my best when leading a team of creative GNAKs (good-natured ass kickers) on an entrepreneurial mission where new technology can make a huge difference in people’s lives.

Clarifying and Learning

Once I had a sense of the goal, the process for attaining it seemed less Herculean. I listed out my “Must Haves” (e.g. creative control, dinner w/ family 4 out of 5 weekdays, intellectual interest) and “Can’t Haves” (e.g. long commute, board members who think they know best, overly crowded market).

I interviewed people with similar early careers, but different paths afterwards. People who had been founding CEOs, but had gone on to become venture capitalists, exec coaches, serial entrepreneurs, social entrepreneurs, nonprofit founders, whiskey-shillers, ranchers and confidence men (last one made up). I looked for people who shared my values and passions, and learned everything I could. Then I listed the most appealing options.

Extreme Narrowing

With list in hand, I jumped into a professional dating period that rivaled Warren Beatty in the 70’s. Lots of good people and ideas, but in Silicon Valley everyone wants to be CEO of their own thing. Also, it’s hard to commit to people you haven’t worked with before – and difficult to get two strangers excited about pursuing the same goals.

Realizing the process was taking too long and going in weird directions, I set the timer and committed to focus. Since then, I have become shark-like in my priorities. No meetings that don’t advance the goal. Always aware of my daily tasks. I even set up a war room in my office for managing priorities and scheduling.

War Room from Dr. Strangelove

War Room from Dr. Strangelove

Since then, I’ve only focused on options that get me excited. These could include starting something from scratch (company, social venture, nonprofit, fund), becoming “Founding CEO” for an early-stage start up, and even taking a shorter term executive role to help companies get to the next level (selling the company, raising a round, etc.).

I’m giving each opportunity a rank of 1-5 in three categories: Gut (do I just want to go do it?), Heart (am I emotionally drawn to it?) and Head (does it make sense to do it?).





Next Action


Sample Gig 1




Conversation with Phil K.

In-person working session

Sample Gig 2




Talk to EIRs

Sample Gig 3




Dinner with Veronica and Tom

Facilitating a meeting would be good path

Sample Gig 4




Need feedback from Steve

Option for shorter term work?

Crab Fishing




Rent boat. Sit in it.

For each line item, I drive hard to a decision. If the opportunity remains interesting to me, I’ll take whatever next steps are required to learn more to bring me closer to a decision.

The best filter I’ve found is to work directly with the team involved. There’s no better way to get to know the opportunity than rolling up your sleeves on something together. This is especially true for new careers – if you’re a mailman and want to be a hand model, best to try it out first.

Final Thoughts

I found it helpful to take time away from all the voices. Too much advice can cloud judgment, and often the advice is what those people would do in your situation, not thoughtful insights into your unique path. (But please keep your comments coming – I’m totally listening.) As a culture, we get so wrapped up in what other people think, it can be hard to find purposeful work. We put too much emphasis on personal brand and image over happiness. It’s a shame. Most people are too busy taking their own selfies to care anyway.

You can be as structured about this process as you want, but my experience is that the gut knows best. The more closely I listen to it, the better the options become.

11 Comments on “From Paralysis to Purpose in 90 Days”

  1. Lesly says:

    Pleased to see how interrogating your Head, Heart and Gut is proving so useful. Awesome!

  2. Jesse says:

    As someone who needs a dungeness connect, it seems to me your process should have been finished with “crab fishing.” Guthearthead, be damned.

  3. Victoria says:

    Hi Dave, Sounds like you have a sound process in place. Wishing you much luck in finding “it.” In the meantime, it occurs to me that this might be a book that would resonate with you, particularly at this stage in your process. Aaron is a good friend of mine. You can read it while crab fishing. 🙂

  4. Dave, very cool process, criteria and exploration … and cool of you to share some of it. Good luck finding the high scorer in all 3 categories!

  5. Hi again Dave! It’s funny how this process is turning into some kind of optimization game. On one side you have assets, on the other you have an expected output. In between those two you have a set of constraints and resources available to you. Let’s play 🙂

    I’ve identified 3 types of assets that are available to you: Experience / Connections / Money -> therefore referred to as “the bucks”

    The resource is mainly how you decide to use your time on a daily basis.

    The constraints are as follows: Limited available time / Blue ocean / People fit / No boss

    Expected output: build a lasting legacy while having fun -> therefore referred to as “the bang”

    Basically, you want to get the most bang for your bucks (you knew this was coming, didn’t you).

    In other words, your above statement is, if not inaccurate, at least very incomplete:

    I’m at my best when leading a team of creative GNAKs (good-natured ass kickers) on an entrepreneurial mission where new technology can make a huge difference in people’s lives… but a happy family is my first priority, I don’t want to change my current habits too much and having to answer to a boss would be somewhat of a letdown.

    TL; DR: “I want to change the world, not my work-life balance”.

    Phrased like this, it is likely that any commercial endeavour would eventually fail your constraints:

    * Interesting but not crowded -> if it’s interesting, it will get crowded and thus you’ll have to move faster and faster
    * Dinner with family 4 out of 5 days / week -> if you want to build something interesting (fun!), useful (legacy!) that also generates money, you’ll have to build it fast and thus probably put in lots of hours of work
    * Legacy-building / high-impact -> as an advisor or a VC, you wouldn’t get the same sense of achievement than as an entrepreneur. Fred Wilson enabled Twitter, he didn’t build the product nor lead the organization.

    Note: I might be wrong about this. Sheryl Sandberg is famously home on evenings and every week-end. But she came in after the “fraternity house” phase of building Facebook was over.

    Looking again at your desirable attributes: something which is not time constrained but where you can bring significant improvements to people’s lives through technology. That sounds a lot like some kind of active philanthropy.

    A tentative conclusion from all this is that it could be something similar to what Bill Gates is doing working on fighting disease. Bill is not time constrained in that his target market won’t be taken by storm by a new entrant 3 months from now, but he has strong self-motivation to find a solution. He’s working on important problems with interesting people. Another example would be Scott McNealy’s funding of the Curriki project, which aims at improving the quality of curricula while decreasing its cost.

    Working on a big problem in a non-profit, you could attract talented people who will also be self-motivated by the vision (therefore matching the “people fit” constraint) while identifying a problem that is currently being overlooked.

    Now obviously a limiting factor is that Bill Gates is pretty much self-funded while you’d probably have to go out and raise money for your own cause. This might cause you to fail the “board members” constraint. As for experience and connections, well, you’d probably find a way to use them effectively in order to reach your goal.

    • djhersh says:

      Thanks, Guillaume. Good analysis, and all issues I’ve thought about before (and why I was getting hung up on it). I have answers though – stay tuned :).

  6. J.D. Mooney says:

    Love the paralysis post, Dave! Had to look up what EIR was, and had 5 seconds of genuine panic for you when Wikipedia told me EIR was a goddess associated with medical skill from Norse Mythology. I thought you fully fucking lost it, you & your norse philosophies….

    That’s not the case….astute & insightful. Love the “what makes you feel most alive?” question….chewing on that heavily here. Keep it coming.

  7. This pairs well with “Always be circumspect.” I enjoy your writing and am glad to be able to keep up with you from my RSS feed reader. I’ve been working on answering the “What’s next?” question for myself these days too.

  8. […] From Paralysis to Purpose in 90 Days → […]

  9. […] my journey to find meaningful work, I struggled a lot with whether to work on a nonprofit. It seemed like the right thing to do, and I […]

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